Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Synthesis of 3-(Benzothiazol-2-yl)-1-Methyl Urea Derivatives and Their Biological Activities

3-(Benzothiazol-2-yl)-1-Methyl Urea 유도체(誘導體)의 합성(合成)과 생리활성(生理活性)에 관(關)한 연구(硏究)

  • Hong, Moo-Ki (Agricultural Chemicals Research Institute, Rural Development Administration) ;
  • Jeong, Young-Ho (Agricultural Chemicals Research Institute, Rural Development Administration) ;
  • Park, Young-Sun (Agricultural Chemicals Research Institute, Rural Development Administration) ;
  • Oh, Se-Mun (Agricultural Chemicals Research Institute, Rural Development Administration)
  • 홍무기 (농촌진흥청 농약연구소) ;
  • 정영호 (농촌진흥청 농약연구소) ;
  • 박영선 (농촌진흥청 농약연구소) ;
  • 오세문 (농촌진흥청 농약연구소)
  • Published : 1987.09.30
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Abstract

Some derivatives of 3-(benzothiazol-2-yl)-1-methyl urea were synthesized by reaction of methyl isocyanate with 2-aminobenzothiazole derivatives prepared by thiocyanation of various substituted anilines. The compounds synthesized were identified by IR, NMR and mass spectra as 3-(5-methyl benzothiazol-2-yl)-1-methyl urea, 3-(5,6-dimethyl benzothiazol-2-yl)-1-methyl urea, 3-(6-ethyl benzothiazol-2-yl)-1-methyl urea, 3-(6-methoxy benzothiazol-2-yl)-1-methyl urea, 3-(6-chloro benzothiazol-2-yl)-1-methyl urea, and 3-(5, 6-dichloro benzothiazol-2-yl)-1-methyl urea. These compounds were subjected to the test for pre-emergence herbicidal activity in the pots with wettable powder formulation. All of these compounds showed pre-emergence herbicidal activity on the grasses (Digitaria adscendens HENR and Setaria viridis P. BEAUV) and broad-leaf weeds (Portulaca oleraces L. and Chenopodium album L.) at the dosage of 800g a.i. per 10a. Of the 6 compounds, 3-(6-ethyl benzothiazol-2-yl)-1-methyl urea showed the highest herbicidal effect on both the grasses and broad-leaf weeds. Even at the rate of 50g a.i. per 10a, this compound inhibited the growth of grasses, selectively.

Aniline 유도체(誘導體)로부터 thiocyanation에 의(依)해 2-aminobenzothiazole 유도체(誘導體)를 합성(合成)하였고, 이어서 mothylisocanate의 부가반응(附加反應)에 의(依)하여 3-(benzothiazol-2-yl)-1-methyl urea 유도체(誘導體) 6종(種)을 합성(合成)하여 IR, NMR, GC/MS 등(等)에 의(依)하여 물질(物質)의 구조(構造)를 확인(確認)하였다. 합성(合成)한 화합물(化合物)들의 바랭이, 강아지풀의 화본과(禾本科) 잡초(雜草)와 쇠비름, 명아주의 광엽(廣葉) 잡초(雜草)에 대(對)하여 50g, 200g, 800g a.i/10a로 발아전처리(發芽前處理)를 하여 살초효과(殺草效果)를 조사(調査)한 결과(結果)는 다음과 같다. 합성(合成)한 화합물(化合物) 6종(種) 모두 발아전처리제(發芽前處理劑)로서 800g a.i/10a 살포량(撒布量)에서 화본과(禾本科) 또는 광엽(廣葉) 잡초(雜草)에 대(對)하여 살초효과(殺草效果)가 인정(認定)되었다. 화합물(化合物) 번호(番號) ACRI-S-8416, ACRI-S-8411 및 ACRI-S-8413은 800g a.i/10a의 살포량(撒布量)에서 광엽(廣葉) 잡초(雜草)에 효과(效果)가 있었으며 ACRI-S-8412는 화본과(禾本科) 잡초(雜草)에 선택적(選擇的) 살초효과(殺草效果)가 인정(認定)되었다. 화합물(化合物) 번호(番號) ACRI-S-8414 즉(卽), 3- (6-ethylbenzothiazol-2-yl)-1-methyl urea는 6종(種)의 화합물(化合物) 중(中) 가장 강력(强力)한 살초효과(殺草效果)를 나타내었으며 50g a.i/10a의 살포량(撒布量)에서도 화본과(禾本科) 잡초(雜草)에 60%의 선택적(選擇的) 살초효과(殺草效果)가 인정(認定)되었다.

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